Triethylamine → 2-amino-N6-(3-iodobenzyl)-9-[beta-D-ribofuranosyl]-adenine

HRID 965192Notes

Reaction equation

[CH:1]1[N:5]([CH:6]2[O:10][CH:9]([CH2:11][OH:12])[CH:8]([OH:13])[CH:7]2[OH:14])[C:4]2[N:15]=[C:16]([NH2:20])[N:17]=[C:18](Cl)[C:3]=2[N:2]=1.Cl.[I:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27].C(N(CC)CC)C>C(O)C>[NH2:20][C:16]1[N:15]=[C:4]2[C:3]([N:2]=[CH:1][N:5]2[C@@H:6]2[O:10][C@H:9]([CH2:11][OH:12])[C@@H:8]([OH:13])[C@H:7]2[OH:14])=[C:18]([NH:27][CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([I:22])[CH:24]=2)[N:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-amino-6-chloropurine riboside (purchased from Aldrich Chemical Co., 80 mg, 0.26 mmol), 3-iodobenzylamine hydrochloride (71.5 mg, 0.265 mmol), and triethylamine (0.11 ml, 0.79 mmol) in ethanol (1.6 ml) was heated for 24 h at 80° C. After the reaction mixture was concentrated to dryness the residue was purified on a silica gel column chromatography (CHCl3 --MeOH, 20:1→10:1) to yield 2-amino-N6 -(3-iodobenzyl)-9-[β-D-ribofuranosyl]-adenine (99 mg, 75%) as a colorless solid: m.p. 152°-154° C.; 1H NMR (DMSO-d6) d 3.52 (m, 1H, H-5'a), 3.63 (m, 1H, H-5'b), 3.89 (m, 1H, H-4'), 4.10 (m, 1H, H-3'), 4.50 (m, 1H, H-2'), 4.60 (br s, 2H, CH2), 5.08 (d, J=4.6 Hz, 1H, exchangeable with D2O, 3'-OH), 5.35 (m, 2H, exchangeable with D2O, 5'- and 2'-OH), 5.73 (d, J=6.2 Hz, 1H, H-1'), 5.83 (br s, 2H, exchangeable with D2O, NH2), 7.11 (pseudo t, J=7.9 and 7.8 Hz, 1H, H-5"), 7.36 (d, J=7.8 Hz, 1H, H-4" or -6"), 7.58 (d, J=7.8 Hz, 1H, H-4" or -6"), 7.70 (s, 1H, H-2"), 7.94 (s, 1H, H-8).

Workup

concentrationAfter the reaction mixture was concentrated to dryness the residue
customwas purified on a silica gel column chromatography (CHCl3 --MeOH, 20:1→10:1)

Sources & evidence

ORD record: ord-095ba296dbff44c1b4b6ed20a3b76ae1
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773423

Reaction notes

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